The Best James Caan Films, Ranked

Elf James Caan, Will Ferrell, Amy Sedaris

With his crooked smile and imposing demeanor, anyone can see how James Caan got cast as Sonny Corleone, even though he’s not Italian. The actor projects toughness, qualities that got him regular work in crime and mafia movies throughout his six-decade career. But Caan had no interest in resting on what came easy. Instead, the actor starred in a wide variety of movies, from kid’s films and Westerns to musicals and comedies. These very different films showed off the impressive range of one of New Hollywood’s greatest talents, as demonstrated in these twenty-five movies.

1 – The Godfather (1972)

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Image Credit: Paramount Pictures.

It might be tempting to say that James Caan has the easiest part in The Godfather, playing the hotheaded oldest Corleone boy, Sonny. After all, his angry, violent tendencies best match the popular perception of gangsters, the type in movies much less ambitious than in Francis Ford Coppola’s film. But Caan finds ways of humanizing the would-be godfather, as when he bites his knuckle after seeing his abused sister Connie (Talia Shire) or gnawing the fingers of his brother-in-law Carlo (Gianni Russo). In those moments, Caan reveals Sonny's childishness, trying to act like a big man in the shadow of his father.

2 – Thief (1981) James Caan

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Image Credit: United Artists.

Michael Mann’s debut film Thief begins with a thrilling sequence of professional bank robbers breaking into a safe. The group works with precision, their stoic professionalism contrasting the neon imagery and psychedelic score from Tangerine Dream. As well-constructed as these moments certainly are, the most memorable scene in Thief involves a simple conversation between safecracker Frank (Caan) and his girlfriend Jessie (Tuesday Weld). In that mundane setting, the couple reveals their vulnerabilities to one another, something far more brave and dangerous than even the most complicated heist.

3 – Misery (1990)

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Image Credit: Columbia Pictures.

Few would confuse James Caan with Stephen King, but the famously gruff actor turned in one of his best performances as a surrogate for the horror author in the Rob Reiner movie Misery. Based on the King novel by the same name, and from a screenplay by William Goldman, Misery finds romance author Paul Sheldon rescued from a car accident by crazed fan Annie (Kathy Bates). Beyond the tale’s insights about the nature of fandom and the perils of the creative process, Misery stands out for the acting feat achieved by Caan, who spends almost the entire film confined to a bed and still creates a complex character.

4 – Brian’s Song (1971)

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Image Credit: Screen Gems.

TV movies rarely match the quality of cinematic releases, especially in the 1970s. But any list of Caan's best work should include Brian’s Song, the inspirational football film co-starring Billy Dee Williams. The true story of football player Brian Piccolo, who befriends Black teammate Gale Sayers (Williams) and battles cancer, threatens to devolve into lazy schmaltz. But even when playing a deathbed scene, Caan drags the film back to reality, grounding his character with a quiet confidence that does not go for easy audience manipulation.

5 – The Rain People (1969)

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Image Credit: Warner Bros. – Seven Arts.

After the disastrous musical Finian’s Rainbow, director Francis Ford Coppola wanted to make a smaller, more realistic movie. That film was The Rain People, the story of a pregnant housewife (Shirley Knight) who goes on a road trip to escape her mundane existence. Along the way, she picks up former college football star “Killer” Killgannon (Caan), whose school and his family abandoned him after he sustained a brain-damaging injury. That setup sounds like a recipe for condescending schlock, but Coppola and especially Caan keep a steady hand on the character, making a fully rounded human being, a person who is so much more than their injury.

6 – The Gambler (1974)

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Image Credit: Paramount Pictures.

Few screenwriting decisions are more fraught than the choice to make the protagonist an academic. Rather than show the story’s themes through action, a screenwriter can just let the professor lecture about big ideas, ensuring that the audience makes the connection. James Toback’s screenplay for The Gambler does veer in this direction, as scholar Axel Freed’s (Caan) descent into gambling addiction mirrors the self-conscious malaise Russian author Fyodor Dostoevsky describes in the novels the professor studies. But with the help of director Karel Reisz, Caan keeps Freed from becoming a plot mechanic, playing up the vulnerable desperation of a man whose troubles are far more than mere academia.

7 – Cloudy With a Chance of Meatballs (2009)

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Image Credit: Sony Pictures Releasing.

The man voiced by Caan in the animated film Cloudy With a Chance of Meatballs doesn’t look anything like the actor and yet feels like a perfect representation of his persona. Stocky, solid, his eyes buried between a permanently lowered brow and a push-broom mustache, Caan’s fisherman Tim Lockwood seems like a gruff guy, completely out of place in Phil Lord and Christopher Miller’s wonderfully surreal take on the children’s book by Judi Barrett and Ron Barrett. And yet, when Tim cracks his stoic facade to express pride in his son, oddball inventor Flint Lockwood (Bill Hader), Caan lets his hardened voice stumble, shading what could have been a simple sentimental moment.

8 – Rollerball (1975)

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Image Credit: United Artists.

Let’s be clear: Rollerball is a very silly movie. Set in the (then) far-off future of 2018, Rollerball focuses on the titular sport, a mix of roller derby, football, and basketball. The sport rewards violence, and as aging star Jonathan E., Caan has more than enough grizzled toughness. But director Norman Jewison and writer William Harrison use the sport as a focal point for what becomes a condemnation of capitalism, reframing Jonathan’s fight to reclaim his former glory as an angry shout against the corporations who turn everyone into grist for their machinery.

9 – The Killer Elite (1976)

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Image Credit: United Artists.

The first reaction of anyone watching The Killer Elite will likely involve the movie’s portrayal of ninjas, the first time the popular Japanese warriors appeared in an American film. But beyond that unlikely element in the story of two former friends turned rival mercenaries (Caan and Robert Duvall) fighting over Japanese dignitaries, The Killer Elite is exactly the type of gritty 70s action movie audiences expect from director Sam Peckinpah. Based on the Robert Syd Hopkins novel Monkey in the Middle and written by Marc Norman and Stirling Silliphant, The Killer Elite gives Caan an unexpectedly rich part, as the first act follows his character Locken’s friendship with Duvall’s Hansen and the second his mental and physical rehabilitation after the betrayal. The dense, dramatic work makes the action all the more compelling—no ninjas required.

10 – Elf (2003)

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Image Credit: New Line Cinema.

James Caan doesn’t seem like a perennial holiday classic type of guy, but many American families watch him every year in the Christmas comedy Elf. And, to be clear, Caan did not enjoy filming the movie, reportedly chafing against star Will Ferrell’s antics. Luckily, the frustration improved Caan’s performance, capturing the irritation of a cold-hearted businessman who learns that not only does he have an adult son, but that the son has been raised by Santa Claus in the North Pole. The exasperated and grumpy Caan makes for the perfect straight man to Farrell’s Buddy the Elf, becoming an unlikely part of Christmas celebrations for generations to come.

11 – El Dorado (1966)

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Image Credit: Lions Gate Home Entertainment.

It’s hard to recall two actors with acting styles more opposed than John Wayne and James Caan. Where the Duke is all swagger and bluster, Caan is quiet rage, tense body language ready to explode at any moment. Despite these differences, the two make a great pair in El Dorado, the Howard Hawks western written by Leigh Brackett. Caan plays Mississippi, a young man on a mission of revenge against the people who killed his father, when he encounters aging gunslinger Cole Thornton (Wayne). The differing acting styles complement one another well, with Caan’s more taciturn approach underscoring Mississippi's barely-bottled rage.

12 – Bottle Rocket (1996)

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Image Credit: Sony Pictures Releasing.

Throughout his career, Texan director Wes Anderson would cast established character actors in surprising roles, getting some career-best work from performers such as Bill Murray, Willem Dafoe, and others. But he started with James Caan, who plays small-time criminal Abe Henry in Anderson’s debut film, the caper comedy Bottle Rocket. Anderson had not yet developed his impeccable sense of design, but the off-beat humor is on full display, especially in Caan’s scenes. Against the heavy he usually gets to play, Caan digs into the goofiness of his crook, perfectly matching the energy of Owen Wilson’s weirdo criminal Dignan.

13 – Les Uns et les Autres (1981)

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Image Credit: Image Entertainment.

It’s hard to think of a more thoroughly American actor than James Caan. And yet, the actor put in some of his best work in the gaudy French film Les Uns et les Autres. As bandleader Jack Glenn, and later, his character’s son Jason, Caan has a dual challenging part, finding notes of humanity in writer/director Claude Lelouch’s dizzying tale about the art community during World War II. Caan can go big when the movie calls for it, and it often does call for outsized performances, but Caan makes the most of subtle pauses his character takes, the furrowed brow when the normally outgoing Glenn men find themselves lost for words.

14 – Funny Lady (1975)

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Image Credit: Columbia Pictures.

Most Barbra Streisand fans don’t rank Funny Lady as high as its 1968 predecessor, Funny Girl, but those who check out the follow-up will find a wonderful performance from Caan. Funny Lady picks up with Fanny Brice (Streisand), having recovered from the heartbreak of losing Nicky Arnstein (Omar Sharif) in the first film, beginning a relationship with producer Billy Rose (Caan). To be honest, the movie itself is a bit of an overstuffed mess, but there’s something thrilling to Caan’s take, which channels his tough-guy persona into a larger-than-life entertainment exec. When he pokes his finger into the chest of some doubting flunky, he retains the menace of Sonny Corleone, even while matching director Herbert Ross’s often outsized tone.

15 – Dogville (2003)

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Image Credit: Lions Gate Home Entertainment.

Some might find Caan a surprising choice for Lars Von Treir’s artificial drama Dogville, in which a community comes together to berate newcomer Grace (Nicole Kidman). Von Trier shoots the movie as if filming a play, with all of the action occurring on a bare stage with minimal props and set dressing. But given his small but important part as a mob boss with a secret connection to Grace, Caan’s filmography and persona work to quickly develop a character. However, Caan does not dial in his glorified cameo. Instead, he plays the quiet menace and finds notes of genuine care in his terrifying gangster, selling Dogville’s dark climax.

16 – Rabbit, Run (1970)

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Image Credit: Warner Bros.

James Caan seems an unlikely pick to play Harry “Rabbit” Angstrom, the aggrieved WASP from John Updike’s novels. A broad-shouldered man of Jewish ancestry, Caan doesn’t look the part of the lanky former high school basketball star who debates Protestant Christianity with a local priest throughout Rabbit, Run, written by Howard B. Kreitsek and directed by Jack Smight. Whatever the physical differences, Caan embodies Harry’s suburban malaise, shooting hoops and visiting his mistress with the weight of a man who has been given every privilege only to find them wanting.

17 – Hide in Plain Sight (1980)

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Image Credit: United Artists.

After spending the 70s building his credibility and clout, Caan finally got the chance to unleash his passion project, the crime drama Hide in Plain Sight, in which he would direct and star. And it did not pay off.

Hide in Plain Sight flopped at the box office and among critics, with many observing how poorly the film handled its exciting narrative about a divorced father who discovers that his ex-wife has married a man hiding from the mob in witness protection. Despite his shortcomings behind the camera, Caan shines in front, capturing the anger and sadness of a man who cannot save his children from a potentially dangerous stepfather.

18 – For the Boys (1991)

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Image Credit: 20th Century Fox.

How could anyone follow up co-starring with Barbra Streisand? For James Caan, he did a movie with Bette Midler (albeit a decade and a half later) in For the Boys. Exercising the muscles he developed during Funny Lady, Caan balances the prickly charm of entertainer Eddie Sparks, who partners with comedienne Dixie Leonard (Midler) on USO tours. Wisely, director Mark Rydell casts Caan as a man who cannot outshine Dixie, and the script from Marshall Brickman, Neal Jiminez, and Lindy Laub gets forward propulsion through the tension between the two.

19 – Countdown (1967)

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Image Credit: Warner Bros – Seven Arts.

No New Hollywood actor worth his salt could resist working with Robert Altman, the iconoclastic yet successful filmmaker. Countdown sits among Altman’s more conventional works, in part because of the power studio Warner Bros. exerted over the final cut, but Caan and frequent collaborator Robert Duvall acquit themselves well as American astronauts racing the Russians to walk on the moon. Despite its global and cosmic stakes, Countdown focuses on the rivalry between Caan and Duvall’s characters and the personal bonds they form while doing their historic work.

20 – Honeymoon in Vegas (1992)

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Image Credit: Warner Bros – Seven Arts.

As this article shows, Caan is no stranger to comedies, but he’s never been more comfortable cracking jokes than he is in Honeymoon in Vegas. Caan plays rich gambler Tommy Korman, who falls at first sight for soon-to-be-married Betsy (Sarah Jessica Parker) and wins her hand in a wager with would-be fiancé Jack (Nicolas Cage). Caan clearly has a ball playing the obstacle to the central romance, taking advantage of every opportunity that writer/director Andrew Bergman gives him to bring a little depth to the over-the-top baddie.

21 – Alien Nation (1988)

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Image Credit: 20th Century Fox.

Naturally, Caan has played as many cops as he has criminals, but he played a new breed in Detective Matthew Sykes, the LAPD veteran paired with newly promoted cop Sam Francisco aka George (Mandy Patinkin). The movies have told myriad stories about bickering partners, but director Graham Baker and writer Rockne S. O’Bannon throw in a twist for Alien Nation, setting the movie in the near future, in which a race of aliens (called “Newcomers”) have become the city’s newest immigrants. In addition to letting Caan play the expected tough-guy notes, especially when grouching at Newcomer George, he also gets to play up the humor of an old-school guy completely out of his depth in a different culture. 

22 – The Yards (2000)

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Image Credit: Buena Vista Pictures.

After launching the career of Wes Anderson, Caan went on to star in the second film from another promising young filmmaker, James Gray. The Yards lacks the sensitivity that Gray brings in his best movies, such as The Lost City of Z or Ad Astra, and co-writer Matt Reeves hasn’t yet developed the sense of wonder that makes his movies The Batman and Dawn of the Planet of the Apes so successful. But the young men get a boost from Caan’s presence in The Yards, playing the stepfather of protagonist Leo (Mark Wahlberg). As a man with shady connections giving tough love to his family, Frank Olchin has much in common with many characters portrayed by Caan in the past. But even when playing a flat, derivative character, Caan controls the screen with his mere presence, a testament to his star power.

23 – Mickey Blue Eyes (1999)

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Image Credit: Warner Bros.

Honeymoon in Vegas might feature Caan’s best comedic performance, but Mickey Blue Eyes shows how far he’s willing to go as the heel of the joke. As the mobster Frank Vitale, whose daughter Gina (Jeanne Tripplehorn) is about to marry Englishman Michael Felgate (Hugh Grant, never more foppish), Caan serves as the threat and straight man in most scenes. Despite that thankless billing, Caan completely goes for it, as when his frustration mounts while trying to get Felgate to say “Fuhgeddaboudit” with a Jersey accent. Nobody’s coming to Mickey Blue Eyes to see Caan, but the movie doesn’t work without him supporting his co-stars.

24 – Queen Bees (2021)

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Image Credit: Gravitas Ventures.

There’s something comforting about the fact that Caan closed out his career not with another mean gangster role, but with a light romantic drama about love late in life. Queen Bees is not even close to the best movie that Caan or co-star Ellen Burstyn has ever made, but it goes down easy, too. Journeyman director Michael Lembeck doesn’t do anything exciting in his cozy flick about shenanigans in a senior home, based on a script from Donald Martin and Harrison Powell, but with a cast that also includes Loretta Devine, Jane Curtin, and Christopher Lloyd, he doesn’t need to. These actors all know what they’re doing, and it’s fun to watch them spend time with their peers.

25 – Sicilian Vampire (2015)

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Image Credit: In Your Ear Productions.

By most standards, Sicilian Vampire is the worst movie in Caan’s otherwise impressive filmography. A vanity project from Canadian food service entrepreneur turned writer/director/star/producer/musician, Frank D’Angelo, Sicilian Vampire has all the hallmarks of a movie made by a man with more money than talent. His character, Sonny, is the most powerful, respected, and well-liked guy who ever existed, able to romance beautiful women and scare even tough guys like Caan and co-star Robert Loggia, especially after becoming a vampire. But few things better demonstrate Caan’s sheer power as a screen presence than putting him in a wholly incompetent film, letting him barely deliver terrible lines, and still command the attention of the audience.